JP2017538284A - Multiple host materials and organic electroluminescent devices comprising the same - Google Patents
Multiple host materials and organic electroluminescent devices comprising the same Download PDFInfo
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- JP2017538284A JP2017538284A JP2017518211A JP2017518211A JP2017538284A JP 2017538284 A JP2017538284 A JP 2017538284A JP 2017518211 A JP2017518211 A JP 2017518211A JP 2017518211 A JP2017518211 A JP 2017518211A JP 2017538284 A JP2017538284 A JP 2017538284A
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- substituted
- unsubstituted
- arylsilyl
- alkyl
- tri
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- 239000000463 material Substances 0.000 title abstract description 61
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 125000003118 aryl group Chemical group 0.000 claims description 53
- 125000005104 aryl silyl group Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 36
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 239000002019 doping agent Substances 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000002950 monocyclic group Chemical group 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 125000001769 aryl amino group Chemical group 0.000 claims description 14
- 125000003367 polycyclic group Chemical group 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000006822 tri(C1-C30) alkylsilyl group Chemical group 0.000 claims description 12
- 125000002723 alicyclic group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 125000006749 (C6-C60) aryl group Chemical group 0.000 claims description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052805 deuterium Inorganic materials 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000005493 quinolyl group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 5
- 125000005549 heteroarylene group Chemical group 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000006743 (C1-C60) alkyl group Chemical group 0.000 claims description 4
- 125000006818 (C3-C60) cycloalkyl group Chemical group 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 4
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 4
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 4
- 125000004934 phenanthridinyl group Chemical group C1(=CC=CC2=NC=C3C=CC=CC3=C12)* 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 229910052710 silicon Inorganic materials 0.000 claims description 4
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- 229910052790 beryllium Inorganic materials 0.000 claims description 3
- 150000004696 coordination complex Chemical class 0.000 claims description 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- 125000005566 carbazolylene group Chemical group 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 3
- 239000010410 layer Substances 0.000 description 84
- -1 aromatic diamine small molecules Chemical class 0.000 description 22
- 238000002347 injection Methods 0.000 description 20
- 239000007924 injection Substances 0.000 description 20
- 230000005525 hole transport Effects 0.000 description 13
- 230000000903 blocking effect Effects 0.000 description 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 230000003247 decreasing effect Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 238000001771 vacuum deposition Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 7
- 125000004429 atom Chemical group 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- 125000005956 isoquinolyl group Chemical group 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 150000004770 chalcogenides Chemical class 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene sulfoxide Natural products C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 150000002220 fluorenes Chemical class 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 229910001507 metal halide Inorganic materials 0.000 description 3
- 150000005309 metal halides Chemical class 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical group FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 description 2
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- 150000004826 dibenzofurans Chemical class 0.000 description 2
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical class C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 description 2
- 125000005509 dibenzothiophenyl group Chemical group 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052762 osmium Inorganic materials 0.000 description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000002344 surface layer Substances 0.000 description 2
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- QTPLEVOKSWEYAC-UHFFFAOYSA-N 1,2-diphenyl-9h-fluorene Chemical compound C=1C=CC=CC=1C1=C2CC3=CC=CC=C3C2=CC=C1C1=CC=CC=C1 QTPLEVOKSWEYAC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical class C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- KCOYLRXCNKJSSC-UHFFFAOYSA-N 9h-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 KCOYLRXCNKJSSC-UHFFFAOYSA-N 0.000 description 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 229910018068 Li 2 O Inorganic materials 0.000 description 1
- 229910003564 SiAlON Inorganic materials 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000005107 alkyl diaryl silyl group Chemical group 0.000 description 1
- 125000005103 alkyl silyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical class CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- ZDZHCHYQNPQSGG-UHFFFAOYSA-N binaphthyl group Chemical group C1(=CC=CC2=CC=CC=C12)C1=CC=CC2=CC=CC=C12 ZDZHCHYQNPQSGG-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001716 carbazoles Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000005105 dialkylarylsilyl group Chemical group 0.000 description 1
- 125000004986 diarylamino group Chemical group 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- 150000002475 indoles Chemical class 0.000 description 1
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- 238000007733 ion plating Methods 0.000 description 1
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000001786 isothiazolyl group Chemical group 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
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- 230000000737 periodic effect Effects 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
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- 150000002910 rare earth metals Chemical class 0.000 description 1
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- 239000010703 silicon Substances 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
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- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
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- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 125000005106 triarylsilyl group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
本発明は、複数のホスト材料及びそれを含む有機電界発光デバイスに関する。複数のホスト化合物の特定の組み合わせを含むことにより、本発明による有機電界発光デバイスは、高効率及び長寿命を提供する。【選択図】なしThe present invention relates to a plurality of host materials and an organic electroluminescent device including the same. By including a specific combination of multiple host compounds, the organic electroluminescent device according to the present invention provides high efficiency and long life. [Selection figure] None
Description
本発明は、複数のホスト材料及びそれを含む有機電界発光デバイスに関する。 The present invention relates to a plurality of host materials and an organic electroluminescent device including the same.
電界発光デバイス（ＥＬデバイス）は、より広い視角、より高いコントラスト比、及びより速い応答時間を提供するという点で利点を有する、自己発光デバイスである。最初の有機ＥＬデバイスは、発光層を形成するための材料として芳香族ジアミン小分子及びアルミニウム錯体を使用することにより、Ｅａｓｔｍａｎ Ｋｏｄａｋによって開発された［Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１，９１３，１９８７］。 Electroluminescent devices (EL devices) are self-emitting devices that have advantages in providing a wider viewing angle, higher contrast ratio, and faster response time. The first organic EL device was developed by Eastman Kodak by using aromatic diamine small molecules and aluminum complexes as materials for forming the emissive layer [Appl. Phys. Lett. 51, 913, 1987].
有機ＥＬデバイス（ＯＬＥＤ）は、有機電界発光材料に電気を印加することにより電気エネルギーを光に変えるデバイスであり、一般にアノード、カソード、及びアノードとカソードとの間の有機層を備えた構造を有する。有機ＥＬデバイスの有機層は、正孔注入層、正孔輸送層、電子阻止層、（ホスト材料及びドーパント材料を含む）発光層、電子緩衝層、正孔阻止層、電子輸送層、電子注入層等から構成されてもよく、有機層に使用される材料は、それらの機能によって、正孔注入材料、正孔輸送材料、電子阻止材料、発光材料、電子緩衝材料、正孔阻止材料、電子輸送材料、電子注入材料等に分類される。有機ＥＬデバイスにおいて、電圧の印加に起因して、正孔がアノードから発光層に注入され、電子がカソードから発光層に注入され、高エネルギーの励起子が正孔と電子との再結合によって形成される。このエネルギーによって、発光有機化合物が励起状態に達し、発光有機化合物の励起状態が基底状態に戻ることに起因してエネルギーから光を発することによって、発光が起こる。 An organic EL device (OLED) is a device that converts electrical energy into light by applying electricity to an organic electroluminescent material, and generally has a structure comprising an anode, a cathode, and an organic layer between the anode and cathode. . The organic layer of the organic EL device includes a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer (including a host material and a dopant material), an electron buffer layer, a hole blocking layer, an electron transport layer, and an electron injection layer. The material used for the organic layer may be composed of a hole injection material, a hole transport material, an electron blocking material, a light emitting material, an electron buffer material, a hole blocking material, an electron transport depending on their functions. It is classified into materials and electron injection materials. In organic EL devices, due to the application of voltage, holes are injected from the anode into the light-emitting layer, electrons are injected from the cathode into the light-emitting layer, and high-energy excitons are formed by recombination of holes and electrons. Is done. By this energy, the luminescent organic compound reaches an excited state, and light emission is caused by emitting light from the energy due to the excited state of the luminescent organic compound returning to the ground state.
有機ＥＬデバイスにおける発光効率を決定する最も重要な要素は、発光材料である。発光材料は、高量子効率、高電子移動度及び正孔移動度を有さなければならず、形成された発光材料層は、均一かつ安定していなければならない。発光材料は、発光の色に応じて、青色発光材料、緑色発光材料、及び赤色発光材料、さらに黄色発光材料または橙色発光材料に分類される。さらに、発光材料は、それらの機能に従って、ホスト材料及びドーパント材料にも分類することができる。近年、高効率及び長寿命を提供する有機ＥＬデバイスの開発が、緊急の課題である。具体的には、ＯＬＥＤの中型または大型パネルのＥＬ特性要件を考慮して、従来のものよりも優れた特性を示す材料が、至急開発されなければならない。固体の状態で溶媒として機能し、エネルギーを伝達するホスト材料は、真空蒸着に適した高純度及び分子量を有する必要がある。さらに、ホスト材料は、熱安定性を達成するための高いガラス転移温度及び高い熱劣化温度、長寿命を達成するための高い電気化学的安定性、非晶質薄膜形成の容易さ、隣接する層の材料への良好な接着、ならびに他の層への非移行性を有する必要がある。 The most important factor that determines the luminous efficiency in the organic EL device is a luminescent material. The light emitting material must have high quantum efficiency, high electron mobility and hole mobility, and the formed light emitting material layer must be uniform and stable. The light emitting material is classified into a blue light emitting material, a green light emitting material, and a red light emitting material, and further, a yellow light emitting material or an orange light emitting material, depending on the color of light emission. Furthermore, luminescent materials can also be classified into host materials and dopant materials according to their function. In recent years, the development of organic EL devices that provide high efficiency and long life has been an urgent issue. Specifically, in view of the EL characteristic requirements of OLED medium or large panels, materials that exhibit properties superior to conventional ones must be urgently developed. A host material that functions as a solvent in a solid state and transmits energy needs to have high purity and molecular weight suitable for vacuum deposition. In addition, the host material has high glass transition temperature and high thermal degradation temperature to achieve thermal stability, high electrochemical stability to achieve long life, easy to form amorphous thin film, adjacent layer Must have good adhesion to the material as well as non-migration to other layers.
発光材料は、色純度、発光効率、及び安定性を向上させるために、ホストとドーパントとの組み合わせとして使用することができる。一般に、優れた特性を有するＥＬデバイスは、ドーパントをホストに注入することにより形成される発光層を備えた構造を有する。ホスト材料は、ドーパント／ホスト材料システムを発光材料として使用するとき、ＥＬデバイスの効率及び寿命に大きく影響を与えるため、ホスト材料の選択は重要である。 The luminescent material can be used as a combination of a host and a dopant in order to improve color purity, luminous efficiency, and stability. In general, an EL device having excellent characteristics has a structure including a light emitting layer formed by injecting a dopant into a host. The choice of host material is important because the host material greatly affects the efficiency and lifetime of the EL device when the dopant / host material system is used as the light emitting material.
国際公開第２０１３／１６８６８８号、欧州特許出願公開第１３２３８０８号、及び国際公開第２０１３／１１２５５７号は、ドーパント／ホスト材料系を含む有機電界発光デバイスを開示する。これらの参考文献では、ホストの中心金属として第２族金属を有する、カルバゾール−カルバゾール構造のホストまたは金属錯体化合物が使用された。しかしながら、これらの参考文献は、金属錯体誘導体と、窒素含有ヘテロアリールを含むカルバゾール誘導体とを含む複数ホストを使用した、有機電界発光デバイスを開示していない。 WO 2013/168688, EP 1323808, and WO 2013/112557 disclose organic electroluminescent devices comprising a dopant / host material system. In these references, a carbazole-carbazole host or metal complex compound having a Group 2 metal as the central metal of the host was used. However, these references do not disclose organic electroluminescent devices using multiple hosts that include metal complex derivatives and carbazole derivatives including nitrogen-containing heteroaryls.
本発明の目的は、高効率及び長寿命を有する有機電界発光デバイスを提供することである。 An object of the present invention is to provide an organic electroluminescent device having high efficiency and long life.
本発明者らは、上記の目的が、アノードとカソードとの間に少なくとも１つの発光層を備える有機電界発光デバイスによって達成され得ることを見出し、ここで発光層は、ホスト及びリン光性ドーパントを含み、ホストは、複数のホスト化合物を含み、複数のホスト化合物のうち少なくとも第１のホスト化合物は、次式（１）によって表わされる金属錯体誘導体であり、第２のホスト化合物は、次式（２）により表され、 The inventors have found that the above objective can be achieved by an organic electroluminescent device comprising at least one light emitting layer between an anode and a cathode, wherein the light emitting layer comprises a host and a phosphorescent dopant. The host includes a plurality of host compounds, and at least the first host compound of the plurality of host compounds is a metal complex derivative represented by the following formula (1), and the second host compound has the following formula ( 2),
式中、
Ｍは、二価金属を表し、
Ｙは、ＯまたはＳを表し、
Ｘは、ＮＲ９、Ｏ、またはＳを表し、
Ｒ１〜Ｒ９は、各々独立して、水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ６０）アルキル、置換もしくは非置換の（Ｃ３−Ｃ６０）シクロアルキル、置換もしくは非置換の（Ｃ６−Ｃ６０）アリール、置換もしくは非置換の４〜６０員ヘテロアリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換のジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のモノもしくはジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは、互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成し、
Where
M represents a divalent metal,
Y represents O or S;
X represents NR 9 , O, or S;
R 1 to R 9 are each independently hydrogen, halogen, cyano, substituted or unsubstituted (C1-C60) alkyl, substituted or unsubstituted (C3-C60) cycloalkyl, substituted or unsubstituted (C6 -C60) aryl, substituted or unsubstituted 4-60 membered heteroaryl, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted Di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, or substituted or unsubstituted mono- or di (C6-C30) arylamino Or at least one selected from nitrogen, oxygen, and sulfur in conjunction with each other Carbon atoms (s) may be replaced by a heteroatom, the monocyclic or polycyclic (C3-C30) to form an alicyclic ring or an aromatic ring,
式中、
Ｍａは、置換もしくは非置換の５〜３０員窒素含有ヘテロアリールを表し、
Ｌａは、単結合、置換もしくは非置換の（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換の３〜３０員ヘテロアリーレンを表し、
Ｘａ〜Ｘｈは、各々独立して、水素、重水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルケニル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルキニル、置換もしくは非置換の（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換の（Ｃ６−Ｃ６０）アリール、置換もしくは非置換の３〜３０員ヘテロアリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換のジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のモノもしくはジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、置換もしくは非置換の、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成し、
ヘテロアリール（エン）は、Ｂ、Ｎ、Ｏ、Ｓ、Ｓｉ、及びＰから選択される少なくとも１個のヘテロ原子を含有する。
Where
Ma represents a substituted or unsubstituted 5- to 30-membered nitrogen-containing heteroaryl,
La represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted 3 to 30 membered heteroarylene,
Xa to Xh are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2 -C30) alkynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, substituted or unsubstituted tri (C1 -C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) Alkyldi (C6-C30) arylsilyl, or substituted or unsubstituted mono- or di (C6-C3) A substituted or unsubstituted, monocyclic ring that represents arylamino or is linked to each other and may be substituted with carbon atom (s) with at least one heteroatom selected from nitrogen, oxygen, and sulfur Forming a cyclic or polycyclic (C3-C30) alicyclic or aromatic ring,
Heteroaryl (ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.
発明の有利な効果
本発明によると、高効率及び長寿命を有する有機電界発光デバイスが提供され、本有機電界発光デバイスを使用した表示デバイスまたは照明デバイスが製造され得る。
Advantageous Effects of the Invention According to the present invention, an organic electroluminescent device having high efficiency and a long lifetime is provided, and a display device or an illumination device using the organic electroluminescent device can be manufactured.
発明の形態
以降、本発明が詳細に記載される。しかしながら、以下の記載は本発明の説明を目的とするものであり、決して本発明の範囲の制限を目的とするものではない。
DETAILED DESCRIPTION OF THE INVENTION Hereinafter, the present invention will be described in detail. However, the following description is for the purpose of illustrating the present invention and is in no way intended to limit the scope of the present invention.
式（１）により表わされる化合物は、次式（３）〜（８）のうちの１つによって表すことができ、 The compound represented by formula (1) can be represented by one of the following formulas (3) to (8):
式中、
Ｍ、Ｙ、Ｘ、及びＲ１〜Ｒ８は、式（１）に定義されたとおりであり、
Ｒ１１〜Ｒ１８、Ｒ１’〜Ｒ８’、及びＲ１１’〜Ｒ１８’は、各々独立して、水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ６０）アルキル、置換もしくは非置換の（Ｃ３−Ｃ６０）シクロアルキル、置換もしくは非置換の（Ｃ６−Ｃ６０）アリール、置換もしくは非置換の４〜６０員ヘテロアリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換のジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のモノもしくはジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは、互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成する。
Where
M, Y, X, and R 1 to R 8 are as defined in formula (1),
R 11 to R 18 , R 1 ′ to R 8 ′, and R 11 ′ to R 18 ′ are each independently hydrogen, halogen, cyano, substituted or unsubstituted (C1-C60) alkyl, substituted or non-substituted. Substituted (C3-C60) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted 4 to 60 membered heteroaryl, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or Unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl Or substituted or unsubstituted mono- or di (C6-C30) arylamino or linked to each other to form nitrogen Forming a monocyclic or polycyclic (C3-C30) alicyclic or aromatic ring, wherein the carbon atom (s) may be substituted with at least one heteroatom selected from oxygen, oxygen, and sulfur To do.
上記の式（１）中、好ましくは、Ｍは、ＢｅまたはＺｎを表し、Ｙは、Ｏを表し、Ｘは、ＮＲ９、Ｏ、またはＳを表し、Ｒ１〜Ｒ９は、各々独立して、水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換の（Ｃ６−Ｃ３０）アリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは、互いと連結して、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成し、より好ましくは、Ｍは、ＢｅまたはＺｎを表し、Ｙは、Ｏを表し、Ｘは、ＮＲ９、Ｏ、またはＳを表し、Ｒ１〜Ｒ９は、各々独立して、水素、ハロゲン、非置換（Ｃ１−Ｃ６）アルキル、非置換またはハロゲンもしくは（Ｃ１−Ｃ６）アルキルで置換された（Ｃ６−Ｃ１５）アリール、置換もしくは非置換のトリ（Ｃ１−Ｃ６）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ１２）アリールシリル、または置換もしくは非置換のジ（Ｃ６−Ｃ１２）アリールアミノを表すか、あるいは、互いと連結して、単環式（Ｃ３−Ｃ１２）芳香族環を形成する。 In the above formula (1), preferably, M represents Be or Zn, Y represents O, X represents NR 9 , O, or S, and R 1 to R 9 are each independently Hydrogen, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted Of tri (C6-C30) arylsilyl, or substituted or unsubstituted di (C6-C30) arylamino, or linked to each other to form a monocyclic or polycyclic (C3-C30) fatty acid Forms a cyclic ring or an aromatic ring, more preferably, M represents Be or Zn, Y represents O, X represents NR 9 , O, or S, and R 1 to R 9 represent Each independently hydrogen, halo Gen, unsubstituted (C1-C6) alkyl, unsubstituted or (C6-C15) aryl substituted with halogen or (C1-C6) alkyl, substituted or unsubstituted tri (C1-C6) alkylsilyl, substituted or unsubstituted Represents substituted tri (C6-C12) arylsilyl, or substituted or unsubstituted di (C6-C12) arylamino, or is linked to each other to form a monocyclic (C3-C12) aromatic ring To do.
上記の式（２）中、Ｌａは、単結合、置換もしくは非置換の（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換の３〜３０員ヘテロアリーレンを表し、好ましくは、単結合、置換もしくは非置換の（Ｃ６−Ｃ１２）アリーレン、または置換もしくは非置換の５〜１５員ヘテロアリーレンを表し、より好ましくは、単結合、非置換またはトリ（Ｃ６−Ｃ１０）アリールシリルもしくは（Ｃ６−Ｃ１２）アリールで置換された（Ｃ６−Ｃ１２）アリーレン、または非置換の６〜１５員ヘテロアリーレンを表す。 In the above formula (2), La represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted 3 to 30-membered heteroarylene, preferably a single bond, substituted or unsubstituted Represents a substituted (C6-C12) arylene, or a substituted or unsubstituted 5-15 membered heteroarylene, more preferably a single bond, unsubstituted or tri (C6-C10) arylsilyl or (C6-C12) aryl. It represents a substituted (C6-C12) arylene or an unsubstituted 6-15 membered heteroarylene.
加えて、Ｌａは、単結合もしくはカルバゾリレンを表してもよく、または次式（９）〜（２１）のうちの１つによって表すことができ、 In addition, La may represent a single bond or carbazolylene, or may be represented by one of the following formulas (9) to (21):
式中、
Ｘｉ〜Ｘｐは、各々独立して、水素、重水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルケニル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルキニル、置換もしくは非置換の（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換の（Ｃ６−Ｃ６０）アリール、置換もしくは非置換の３〜３０員ヘテロアリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換のジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のモノもしくはジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは、互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、置換もしくは非置換の、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成し、好ましくは、各々独立して、水素、シアノ、置換もしくは非置換の（Ｃ６−Ｃ１５）アリール、置換もしくは非置換の１０〜２０員ヘテロアリール、または置換もしくは非置換のトリ（Ｃ６−Ｃ１０）アリールシリルを表し、より好ましくは、各々独立して、水素、シアノ、非置換もしくはトリ（Ｃ６−Ｃ１０）アリールシリルで置換された（Ｃ６−Ｃ１５）アリール、または非置換もしくは（Ｃ６−Ｃ１５）アリールで置換された１０〜２０員ヘテロアリールを表す。
Where
Xi to Xp are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2 -C30) alkynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, substituted or unsubstituted tri (C1 -C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) Alkyldi (C6-C30) arylsilyl, or substituted or unsubstituted mono- or di (C6-C3) ) Represents an arylamino or, in conjunction with each other, a substituted or unsubstituted, single, optionally substituted carbon atom (s) with at least one heteroatom selected from nitrogen, oxygen, and sulfur Forming a cyclic or polycyclic (C3-C30) alicyclic or aromatic ring, preferably each independently of hydrogen, cyano, substituted or unsubstituted (C6-C15) aryl, substituted or Represents unsubstituted 10-20 membered heteroaryl, or substituted or unsubstituted tri (C6-C10) arylsilyl, more preferably each independently hydrogen, cyano, unsubstituted or tri (C6-C10) aryl It represents (C6-C15) aryl substituted with silyl, or 10-20 membered heteroaryl unsubstituted or substituted with (C6-C15) aryl.
上記の式（２）中、Ｍａは、置換もしくは非置換の５〜３０員窒素含有ヘテロアリールを表し、好ましくは、置換もしくは非置換の６〜１０員窒素含有ヘテロアリールを表し、より好ましくは、非置換（Ｃ６−Ｃ２５）アリール、シアノで置換された（Ｃ６−Ｃ１２）アリール、（Ｃ１−Ｃ６）アルキルで置換された（Ｃ６−Ｃ１２）アリール、トリ（Ｃ６−Ｃ１２）アリールシリルで置換された（Ｃ６−Ｃ１２）アリール、非置換６〜１５員ヘテロアリール、及び（Ｃ６−Ｃ１２）アリールで置換された６〜１５員ヘテロアリールからなる群から選択される置換基で置換された、６〜１０員窒素含有ヘテロアリールを表す。 In the above formula (2), Ma represents a substituted or unsubstituted 5- to 30-membered nitrogen-containing heteroaryl, preferably a substituted or unsubstituted 6- to 10-membered nitrogen-containing heteroaryl, and more preferably, Unsubstituted (C6-C25) aryl, (C6-C12) aryl substituted with cyano, (C6-C12) aryl substituted with (C1-C6) alkyl, substituted with tri (C6-C12) arylsilyl 6-10 substituted with a substituent selected from the group consisting of (C6-C12) aryl, unsubstituted 6-15 membered heteroaryl, and 6-15 membered heteroaryl substituted with (C6-C12) aryl Represents a member nitrogen-containing heteroaryl.
加えて、Ｍａは、置換もしくは非置換のピロリル、置換もしくは非置換のイミダゾリル、置換もしくは非置換のピラゾリル、置換もしくは非置換のトリアジニル、置換もしくは非置換のテトラジニル、置換もしくは非置換のトリアゾリル、置換もしくは非置換のテトラゾリル、置換もしくは非置換のピリジル、置換もしくは非置換のピラジニル、置換もしくは非置換のピリミジニル、置換もしくは非置換のピリダジニル等の単環式環型ヘテロアリール、または、置換もしくは非置換のベンズイミダゾリル、置換もしくは非置換のイソインドリル、置換もしくは非置換のインドリル、置換もしくは非置換のインダゾリル、置換もしくは非置換のベンゾチアジアゾリル、置換もしくは非置換のキノリル、置換もしくは非置換のイソキノリル、置換もしくは非置換のシンノリニル、置換もしくは非置換のキナゾリニル、置換もしくは非置換のナフチリジニル、置換もしくは非置換のキノキサリニル、置換もしくは非置換のカルバゾリル、置換もしくは非置換のフェナントリジニル等の縮合環型ヘテロアリールを表してもよい。好ましくは、Ｍａは、置換もしくは非置換のトリアジニル、置換もしくは非置換のピリミジニル、置換もしくは非置換のピリジル、置換もしくは非置換のキノリル、置換もしくは非置換のイソキノリル、置換もしくは非置換のキナゾリニル、置換もしくは非置換のナフチリジニル、または置換もしくは非置換のキノキサリニルを表し得る。Ｍａにおいて、置換ピロリル等の置換基は、（Ｃ６−Ｃ２５）アリール、シアノで置換された（Ｃ６−Ｃ１２）アリール、（Ｃ１−Ｃ６）アルキルで置換された（Ｃ６−Ｃ１２）アリール、トリ（Ｃ６−Ｃ１２）アリールシリルで置換された（Ｃ６−Ｃ１２）アリール、シアノ、（Ｃ１−Ｃ６）アルキル、トリ（Ｃ６−Ｃ１２）アリールシリル、６〜１５員ヘテロアリール、または（Ｃ６−Ｃ１２）アリールで置換された６〜１５員ヘテロアリール、具体的には、シアノ、（Ｃ１−Ｃ６）アルキル、フェニル、ビフェニル、テルフェニル、ナフチル、フェニルナフチル、ナフチルフェニル、ジフェニルフルオレン、フェナントレニル、アントラセニル、ジベンゾチオフェニル、ジベンゾフラニル、あるいは非置換またはシアノ、（Ｃ１−Ｃ６）アルキル、もしくはトリフェニルシリルで置換されたフェニルカルバゾリルであってもよい。 In addition, Ma is substituted or unsubstituted pyrrolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted tetrazinyl, substituted or unsubstituted triazolyl, substituted or Monocyclic ring heteroaryl such as unsubstituted tetrazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridazinyl, or substituted or unsubstituted benz Imidazolyl, substituted or unsubstituted isoindolyl, substituted or unsubstituted indolyl, substituted or unsubstituted indazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted Or substituted cinnolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted carbazolyl, substituted or unsubstituted phenanthridinyl, etc. Aryl may be represented. Preferably, Ma is substituted or unsubstituted triazinyl, substituted or unsubstituted pyrimidinyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolyl, substituted or unsubstituted isoquinolyl, substituted or unsubstituted quinazolinyl, substituted or It may represent unsubstituted naphthyridinyl or substituted or unsubstituted quinoxalinyl. In Ma, substituents such as substituted pyrrolyl are (C6-C25) aryl, (C6-C12) aryl substituted with cyano, (C6-C12) aryl substituted with (C1-C6) alkyl, tri (C6 -C12) substituted with (C6-C12) aryl, cyano, (C1-C6) alkyl, tri (C6-C12) arylsilyl, 6-15 membered heteroaryl, or (C6-C12) aryl substituted with arylsilyl 6-15 membered heteroaryls, specifically, cyano, (C1-C6) alkyl, phenyl, biphenyl, terphenyl, naphthyl, phenylnaphthyl, naphthylphenyl, diphenylfluorene, phenanthrenyl, anthracenyl, dibenzothiophenyl, dibenzo Furanyl, or unsubstituted or cyano, (C1-C6 Alkyl, or it may be a phenylcarbazolyl substituted with triphenylsilyl.
上記の式（２）中、Ｘａ〜Ｘｈは、各々独立して、水素、重水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルケニル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルキニル、置換もしくは非置換の（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換の（Ｃ６−Ｃ６０）アリール、置換もしくは非置換の３〜３０員ヘテロアリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換のジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のモノもしくはジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは、互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、置換もしくは非置換の、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成し、好ましくは、各々独立して、水素、シアノ、置換もしくは非置換の（Ｃ６−Ｃ１５）アリール、置換もしくは非置換の１０〜２０員ヘテロアリール、または置換もしくは非置換のトリ（Ｃ６−Ｃ１０）アリールシリルを表すか、あるいは、互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、置換もしくは非置換の、単環式もしくは多環式の（Ｃ６−Ｃ２０）芳香族環を形成する。より好ましくは、Ｘａ〜Ｘｈは、各々独立して、水素；シアノ；非置換または１０〜２０員ヘテロアリールもしくはトリ（Ｃ６−Ｃ１０）アリールシリルで置換された（Ｃ６−Ｃ１５）アリール；非置換または（Ｃ６−Ｃ１２）アリールもしくはシアノ（Ｃ６−Ｃ１２）アリールで置換された１０〜２０員ヘテロアリール；または非置換トリ（Ｃ６−Ｃ１０）アリールシリルを表すか、あるいは、互いと連結して、置換もしくは非置換のベンゼン、置換もしくは非置換のインドール、置換もしくは非置換のベンゾインドール、置換もしくは非置換のインデン、置換もしくは非置換のベンゾフラン、または置換もしくは非置換のベンゾチオフェンを形成する。 In the above formula (2), Xa to Xh are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl. Substituted, unsubstituted (C2-C30) alkynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, Substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or Unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, or substituted or unsubstituted mono Represents di (C6-C30) arylamino or linked to each other, the carbon atom (s) may be substituted with at least one heteroatom selected from nitrogen, oxygen, and sulfur Or an unsubstituted, monocyclic or polycyclic (C3-C30) alicyclic or aromatic ring, preferably each independently of hydrogen, cyano, substituted or unsubstituted (C6- C15) represents aryl, substituted or unsubstituted 10-20 membered heteroaryl, or substituted or unsubstituted tri (C6-C10) arylsilyl, or selected from nitrogen, oxygen, and sulfur linked to each other To form a substituted or unsubstituted monocyclic or polycyclic (C6-C20) aromatic ring in which the carbon atom (s) may be substituted with at least one heteroatom. More preferably, Xa-Xh are each independently hydrogen; cyano; unsubstituted or (C6-C15) aryl substituted with 10-20 membered heteroaryl or tri (C6-C10) arylsilyl; unsubstituted or 10- to 20-membered heteroaryl substituted with (C6-C12) aryl or cyano (C6-C12) aryl; or unsubstituted tri (C6-C10) arylsilyl, or linked to each other, substituted or Forms unsubstituted benzene, substituted or unsubstituted indole, substituted or unsubstituted benzoindole, substituted or unsubstituted indene, substituted or unsubstituted benzofuran, or substituted or unsubstituted benzothiophene.
本明細書において、「（Ｃ１−Ｃ３０）アルキル」は、炭素原子の数が好ましくは１〜２０個、より好ましくは１〜１０個である鎖を構成する１〜３０個の炭素原子を有する直鎖もしくは分岐鎖アルキルを意図し、メチル、エチル、ｎ−プロピル、イソプロピル、ｎ−ブチル、イソブチル、ｔｅｒｔ−ブチル等を含み、「（Ｃ２−Ｃ３０）アルケニル」は、炭素原子の数が好ましくは２〜２０個、より好ましくは２〜１０個である鎖を構成する２〜３０個の炭素原子を有する直鎖もしくは分岐鎖アルケニルを意図し、ビニル、１−プロペニル、２−プロペニル、１−ブテニル、２−ブテニル、３−ブテニル、２−メチルブタ−２−エニル等を含み、「（Ｃ２−Ｃ３０）アルキニル」は、炭素原子の数が好ましくは２〜２０個、より好ましくは２〜１０個である鎖を構成する２〜３０個の炭素原子を有する直鎖もしくは分岐鎖アルキニルを意図し、エチニル、１−プロピニル、２−プロピニル、１−ブチニル、２−ブチニル、３−ブチニル、１−メチルペンタ−２−イニル等を含み、「（Ｃ３−Ｃ３０）シクロアルキル」は、炭素原子の数が好ましくは３〜２０個、より好ましくは３〜７個である３〜３０個の環骨格炭素原子を有する単環式もしくは多環式の炭化水素であり、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル等を含み、「３〜７員ヘテロシクロアルキル」は、Ｂ、Ｎ、Ｏ、Ｓ、Ｓｉ、及びＰ、好ましくはＯ、Ｓ、及びＮから選択される少なくとも１個のヘテロ原子を含む、３〜７個、好ましくは５〜７個の環骨格原子を有するシクロアルキルであり、テトラヒドロフラン、ピロリジン、チオラン、テトラヒドロピラン等を含み、「（Ｃ６−Ｃ３０）アリール（エン）」は、炭素原子の数が好ましくは６〜２０個、より好ましくは６〜１５個である６〜３０個の環骨格炭素原子を有する芳香族炭化水素から誘導された単環式環または縮合環であり、フェニル、ビフェニル、テルフェニル、ナフチル、ビナフチル、フェニルナフチル、ナフチルフェニル、フルオレニル、フェニルフルオレニル、ベンゾフルオレニル、ジベンゾフルオレニル、フェナントレニル、フェニルフェナントレニル、アントラセニル、インデニル、トリフェニレニル、ピレニル、テトラセニル、ペリレニル、クリセニル、ナフタセニル、フルオランテニル等を含み、「３〜３０員ヘテロアリール」は、Ｂ、Ｎ、Ｏ、Ｓ、Ｓｉ、及びＰからなる群から選択される少なくとも１個、好ましくは１〜４個のヘテロ原子を含む、３〜３０個の環骨格原子、好ましくは３〜２０個の環骨格原子、より好ましくは３〜１５個の環骨格原子を有するアリールであり、単環式環、または少なくとも１つのベンゼン環と縮合した縮合環であり、部分的に飽和していてもよく、単結合（複数可）を介して少なくとも１つのヘテロアリールまたはアリール基をヘテロアリール基に連結させることによって形成されるものであってもよく、フリル、チオフェニル、ピロリル、イミダゾリル、ピラゾリル、チアゾリル、チアジアゾリル、イソチアゾリル、イソオキサゾリル、オキサゾリル、オキサジアゾリル、トリアジニル、テトラジニル、トリアゾリル、テトラゾリル、フラザニル、ピリジル、ピラジニル、ピリミジニル、ピリダジニル等を含む単環式環型ヘテロアリール、及びベンゾフラニル、ベンゾチオフェニル、イソベンゾフラニル、ジベンゾフラニル、ジベンゾチオフェニル、ベンズイミダゾリル、ベンゾチアゾリル、ベンゾイソチアゾリル、ベンゾイソオキサゾリル、ベンゾオキサゾリル、イソインドリル、インドリル、ベンゾインドリル、インダゾリル、ベンゾチアジアゾリル、キノリル、イソキノリル、シンノリニル、キナゾリニル、キノキサリニル、カルバゾリル、フェノキサジニル、フェナントリジニル、ベンゾジオキソリル等を含む縮合環型ヘテロアリールを含み、「窒素含有５〜３０員ヘテロアリール」は、少なくとも１個のヘテロ原子Ｎを含む、５〜３０個、好ましくは５〜２０個、より好ましくは５〜１５個の環骨格原子を有するアリールであり、単環式環、または少なくとも１つのベンゼン環と縮合した縮合環であり、部分的に飽和していてもよく、単結合（複数可）を介して少なくとも１つのヘテロアリールまたはアリール基をヘテロアリール基に連結させることによって形成されるものであってもよく、ピロリル、イミダゾリル、ピラゾリル、トリアジニル、テトラジニル、トリアゾリル、テトラゾリル、ピリジル、ピラジニル、ピリミジニル、ピリダジニル等を含む単環式環型ヘテロアリール、及びベンズイミダゾリル、イソインドリル、インドリル、インダゾリル、ベンゾチアジアゾリル、キノリル、イソキノリル、シンノリニル、キナゾリニル、キノキサリニル、カルバゾリル、フェナントリジニル等を含む縮合環型ヘテロアリールを含む。さらに、「ハロゲン」は、Ｆ、Ｃｌ、Ｂｒ、及びＩを含む。 In the present specification, “(C1-C30) alkyl” means a straight chain having 1 to 30 carbon atoms constituting a chain having preferably 1 to 20 carbon atoms, more preferably 1 to 10 carbon atoms. Contemplated as a chain or branched chain alkyl, including methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, etc. “(C2-C30) alkenyl” preferably has 2 carbon atoms. Contemplated are straight chain or branched alkenyl having 2 to 30 carbon atoms constituting a chain of ˜20, more preferably 2 to 10, vinyl, 1-propenyl, 2-propenyl, 1-butenyl, Including 2-butenyl, 3-butenyl, 2-methylbut-2-enyl and the like, "(C2-C30) alkynyl" preferably has 2 to 20 carbon atoms, more preferably Intended for straight-chain or branched alkynyl having 2 to 30 carbon atoms constituting a chain of 10 to ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like, and “(C3-C30) cycloalkyl” is preferably a ring skeleton having 3 to 30 carbon atoms, preferably 3 to 20 carbon atoms, more preferably 3 to 7 carbon atoms. Monocyclic or polycyclic hydrocarbons having carbon atoms, including cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., and “3-7 membered heterocycloalkyl” includes B, N, O, S, Si, And P, preferably cycloalkyl having 3 to 7, preferably 5 to 7 ring skeleton atoms, containing at least one heteroatom selected from O, S and N Including tetrahydrofuran, pyrrolidine, thiolane, tetrahydropyran and the like, “(C6-C30) aryl (ene)” is preferably 6 to 30 carbon atoms having 6 to 20 carbon atoms, more preferably 6 to 15 carbon atoms. A monocyclic ring or a condensed ring derived from an aromatic hydrocarbon having a ring skeleton carbon atom of phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, fluorenyl, phenylfluorenyl, benzo Fluorenyl, dibenzofluorenyl, phenanthrenyl, phenylphenanthrenyl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, chrycenyl, naphthacenyl, fluoranthenyl, etc., and "3 to 30 membered heteroaryl" B, N, O, S, S 3 to 30 ring skeleton atoms, preferably 3 to 20 ring skeleton atoms, more preferably at least one, preferably 1 to 4 heteroatoms selected from the group consisting of i and P An aryl having 3 to 15 ring skeleton atoms, a monocyclic ring, or a condensed ring condensed with at least one benzene ring, which may be partially saturated, with a single bond (s) Which may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group via furyl, thiophenyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl , Triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyri Monocyclic ring heteroaryls, including benzofuranyl, benzothiophenyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzoisothiazolyl, benzoiso Condensation including oxazolyl, benzoxazolyl, isoindolyl, indolyl, benzoindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenoxazinyl, phenanthridinyl, benzodioxolyl Including cyclic heteroaryl, “nitrogen containing 5-30 membered heteroaryl” contains 5-30, preferably 5-20, more preferably 5 containing at least one heteroatom N. An aryl having 15 ring skeleton atoms, a monocyclic ring, or a condensed ring fused with at least one benzene ring, which may be partially saturated, via a single bond (s) It may be formed by linking at least one heteroaryl or aryl group to a heteroaryl group, such as pyrrolyl, imidazolyl, pyrazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, etc. Monocyclic cyclic heteroaryls including and condensed ring heteroaryls including benzimidazolyl, isoindolyl, indolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnolinyl, quinazolinyl, quinoxalinyl, carbazolyl, phenanthridinyl, etc. Including Further, “halogen” includes F, Cl, Br, and I.
本明細書において、「置換もしくは非置換の」という表現における「置換」とは、ある特定の官能基内の水素原子が、別の原子または基、すなわち置換基で置換されることを意味する。式中の置換アルキル（エン）、置換アルケニル、置換アルキニル、置換シクロアルキル、置換アリール（エン）、置換ヘテロアリール、置換トリアルキルシリル、置換トリアリールシリル、置換ジアルキルアリールシリル、置換アルキルジアリールシリル、置換モノもしくはジアリールアミノ、または置換単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環の置換基は、各々独立して、重水素、ハロゲン、シアノ、カルボキシル、ニトロ、ヒドロキシル、（Ｃ１−Ｃ３０）アルキル、ハロ（Ｃ１−Ｃ３０）アルキル、（Ｃ２−Ｃ３０）アルケニル、（Ｃ２−Ｃ３０）アルキニル、（Ｃ１−Ｃ３０）アルコキシ、（Ｃ１−Ｃ３０）アルキルチオ、（Ｃ３−Ｃ３０）シクロアルキル、（Ｃ３−Ｃ３０）シクロアルケニル、３〜７員ヘテロシクロアルキル、（Ｃ６−Ｃ３０）アリールオキシ、（Ｃ６−Ｃ３０）アリールチオ、非置換または（Ｃ６−Ｃ３０）アリールで置換された３〜３０員ヘテロアリール、非置換またはシアノ、３〜３０員ヘテロアリール、もしくはトリ（Ｃ６−Ｃ３０）アリールシリルで置換された（Ｃ６−Ｃ３０）アリール、トリ（Ｃ１−Ｃ３０）アルキルシリル、トリ（Ｃ６−Ｃ３０）アリールシリル、ジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、アミノ、モノもしくはジ（Ｃ１−Ｃ３０）アルキルアミノ、モノもしくはジ（Ｃ６−Ｃ３０）アリールアミノ、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールアミノ、（Ｃ１−Ｃ３０）アルキルカルボニル、（Ｃ１−Ｃ３０）アルコキシカルボニル、（Ｃ６−Ｃ３０）アリールカルボニル、ジ（Ｃ６−Ｃ３０）アリールボロニル、ジ（Ｃ１−Ｃ３０）アルキルボロニル、（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールボロニル、（Ｃ６−Ｃ３０）アリール（Ｃ１−Ｃ３０）アルキル、及び（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールからなる群から選択される少なくとも１つであり、好ましくは、ハロゲン、シアノ、（Ｃ１−Ｃ６）アルキル、非置換または（Ｃ６−Ｃ１２）アリールで置換された５〜１５員ヘテロアリール、非置換またはシアノ、（Ｃ６−Ｃ１２）アリール、もしくはトリ（Ｃ６−Ｃ１２）アリールシリルで置換された（Ｃ６−Ｃ２５）アリール、トリ（Ｃ６−Ｃ１２）アリールシリル、及び（Ｃ１−Ｃ６）アルキル（Ｃ６−Ｃ１２）アリールからなる群から選択される少なくとも１つである。 In the present specification, the term “substituted” in the expression “substituted or unsubstituted” means that a hydrogen atom in a specific functional group is substituted with another atom or group, that is, a substituent. In the formula, substituted alkyl (ene), substituted alkenyl, substituted alkynyl, substituted cycloalkyl, substituted aryl (ene), substituted heteroaryl, substituted trialkylsilyl, substituted triarylsilyl, substituted dialkylarylsilyl, substituted alkyldiarylsilyl, substituted Mono or diarylamino, or substituted monocyclic or polycyclic (C3-C30) alicyclic or aromatic substituents are each independently deuterium, halogen, cyano, carboxyl, nitro, hydroxyl , (C1-C30) alkyl, halo (C1-C30) alkyl, (C2-C30) alkenyl, (C2-C30) alkynyl, (C1-C30) alkoxy, (C1-C30) alkylthio, (C3-C30) cyclo Alkyl, (C3-C30) cycloalkenyl, 3-7 members Terocycloalkyl, (C6-C30) aryloxy, (C6-C30) arylthio, unsubstituted or substituted with (C6-C30) aryl, 3-30 membered heteroaryl, unsubstituted or cyano, 3-30 membered heteroaryl Or (C6-C30) aryl, tri (C1-C30) alkylsilyl, tri (C6-C30) arylsilyl, di (C1-C30) alkyl (C6-C30) substituted with tri (C6-C30) arylsilyl ) Arylsilyl, (C1-C30) alkyldi (C6-C30) arylsilyl, amino, mono or di (C1-C30) alkylamino, mono or di (C6-C30) arylamino, (C1-C30) alkyl (C6) -C30) arylamino, (C1-C30) alkylcarbonyl, ( 1-C30) alkoxycarbonyl, (C6-C30) arylcarbonyl, di (C6-C30) aryl boronyl, di (C1-C30) alkyl boronyl, (C1-C30) alkyl (C6-C30) aryl boronyl, It is at least one selected from the group consisting of (C6-C30) aryl (C1-C30) alkyl and (C1-C30) alkyl (C6-C30) aryl, preferably halogen, cyano, (C1-C6 ) Alkyl, unsubstituted or 5- to 15-membered heteroaryl substituted with (C6-C12) aryl, unsubstituted or substituted with cyano, (C6-C12) aryl, or tri (C6-C12) arylsilyl (C6) -C25) aryl, tri (C6-C12) arylsilyl, and (C1-C6) alkyl ( C6-C12) at least one selected from the group consisting of aryl.
式（１）により表される第１のホスト化合物には、以下の化合物が含まれるが、これらに限定されない。 The first host compound represented by formula (1) includes, but is not limited to, the following compounds:
式（２）により表される第２のホスト化合物には、以下の化合物が含まれるが、これらに限定されない。 The second host compound represented by formula (2) includes, but is not limited to, the following compounds:
本発明による有機電界発光デバイスは、アノード、カソード、及びアノードとカソードとの間の少なくとも１つの有機層を備える。この有機層は、発光層を含み、発光層は、ホスト及びリン光ドーパントを含む。ホスト材料は、複数のホスト化合物を含み、複数のホスト化合物のうち少なくとも第１のホスト化合物は、式（１）により表され、第２のホスト化合物は、式（２）により表される。 The organic electroluminescent device according to the present invention comprises an anode, a cathode, and at least one organic layer between the anode and the cathode. The organic layer includes a light emitting layer, and the light emitting layer includes a host and a phosphorescent dopant. The host material includes a plurality of host compounds, and at least the first host compound among the plurality of host compounds is represented by the formula (1), and the second host compound is represented by the formula (2).
発光層は、光が放出される層であり、単層であっても、２つ以上の層が積層された多層であってもよい。発光層において、ホスト化合物に基づくドーパント化合物のドーピング濃度は２０重量％未満であることが望ましい。 The light emitting layer is a layer from which light is emitted, and may be a single layer or a multilayer in which two or more layers are stacked. In the light emitting layer, the doping concentration of the dopant compound based on the host compound is desirably less than 20% by weight.
有機層は発光層を含み、正孔注入層、正孔輸送層、電子輸送層、電子注入層、中間層、正孔阻止層、及び電子阻止層からなる群から選択される少なくとも１つの層をさらに含んでもよい。 The organic layer includes a light emitting layer, and includes at least one layer selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Further, it may be included.
本発明の有機電界発光デバイスによると、第１のホスト材料と第２のホスト材料との重量比は、１：９９〜９９：１の範囲内である。 According to the organic electroluminescent device of the present invention, the weight ratio of the first host material and the second host material is in the range of 1:99 to 99: 1.
ドーパントは、好ましくは少なくとも１つのリン光性ドーパントである。本発明による有機電界発光デバイスに適用されるドーパント材料は、限定されるものではないが、好ましくは、イリジウム、オスミウム、銅、及び白金の金属化錯体化合物から選択され得、より好ましくは、イリジウム、オスミウム、銅、及び白金のオルト金属化錯体化合物から選択され得、さらにより好ましくは、オルト金属化イリジウム錯体化合物から選択され得る。 The dopant is preferably at least one phosphorescent dopant. The dopant material applied to the organic electroluminescent device according to the present invention is not limited, but may preferably be selected from iridium, osmium, copper and platinum metallized complex compounds, more preferably iridium, It may be selected from ortho-metalated complex compounds of osmium, copper, and platinum, and even more preferably selected from ortho-metalated iridium complex compounds.
リン光性ドーパントは、好ましくは、次式（１０１）〜（１０３）により表わされる化合物から選択される。 The phosphorescent dopant is preferably selected from compounds represented by the following formulas (101) to (103).
式中、Ｌは、以下の構造から選択され、 Where L is selected from the following structures:
Ｒ１００は、水素、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキル、または置換もしくは非置換の（Ｃ３−Ｃ３０）シクロアルキルを表し、
Ｒ１０１〜Ｒ１０９、及びＲ１１１〜Ｒ１２３は、各々独立して、水素、重水素、ハロゲン、非置換もしくはハロゲン（複数可）で置換された（Ｃ１−Ｃ３０）アルキル、シアノ、置換もしくは非置換の（Ｃ１−Ｃ３０）アルコキシ、置換もしくは非置換の（Ｃ６−Ｃ３０）アリール、または置換もしくは非置換の（Ｃ３−Ｃ３０）シクロアルキルを表し、Ｒ１０６〜Ｒ１０９の隣接する置換基は、互いと連結して、置換もしくは非置換の縮合環、例えば、非置換もしくはアルキルで置換されたフルオレン、非置換もしくはアルキルで置換されたジベンゾチオフェン、または非置換もしくはアルキルで置換されたジベンゾフランを形成してもよく、Ｒ１２０〜Ｒ１２３の隣接する置換基は、互いと連結して、置換もしくは非置換の縮合環、例えば、非置換またはアルキルもしくはアリールで置換されたキノリンを形成してもよく、
Ｒ１２４〜Ｒ１２７は、各々独立して、水素、重水素、ハロゲン、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキル、または置換もしくは非置換の（Ｃ６−Ｃ３０）アリールを表し、Ｒ１２４〜Ｒ１２７の隣接する置換基は、互いと連結して、置換もしくは非置換の縮合環、例えば、非置換もしくはアルキルで置換されたフルオレン、非置換もしくはアルキルで置換されたジベンゾチオフェン、または非置換もしくはアルキルで置換されたジベンゾフランを形成してもよく、
Ｒ２０１〜Ｒ２１１は、各々独立して、水素、重水素、ハロゲン、非置換もしくはハロゲン（複数可）で置換された（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換の（Ｃ３−Ｃ３０）シクロアルキル、または置換もしくは非置換の（Ｃ６−Ｃ３０）アリールを表し、Ｒ２０８〜Ｒ２１１の隣接する置換基は、互いと連結して、置換もしくは非置換の縮合環、例えば、非置換もしくはアルキルで置換されたフルオレン、非置換もしくはアルキルで置換されたジベンゾチオフェン、または非置換もしくはアルキルで置換されたジベンゾフランを形成してもよく、
ｒ及びｓは、各々独立して、１〜３の整数を表し、ｒまたはｓが２以上の整数である場合、Ｒ１００の各々は、同じでも異なっていてもよく、
ｅは、１〜３の整数を表す。
R 100 represents hydrogen, substituted or unsubstituted (C1-C30) alkyl, or substituted or unsubstituted (C3-C30) cycloalkyl,
R 101 -R 109 and R 111 -R 123 are each independently (C1-C30) alkyl, cyano, substituted or non-substituted with hydrogen, deuterium, halogen, unsubstituted or substituted with halogen (s). Represents substituted (C1-C30) alkoxy, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (C3-C30) cycloalkyl, wherein adjacent substituents of R 106 to R 109 are To form a substituted or unsubstituted fused ring, for example, unsubstituted or alkyl-substituted fluorene, unsubstituted or alkyl-substituted dibenzothiophene, or unsubstituted or alkyl-substituted dibenzofuran. The adjacent substituents of R 120 to R 123 may be linked to each other to form a substituted or unsubstituted contraction. May form a quinoline, for example unsubstituted or substituted with alkyl or aryl,
R 124 to R 127 each independently represents hydrogen, deuterium, halogen, substituted or unsubstituted (C 1 -C 30) alkyl, or substituted or unsubstituted (C 6 -C 30) aryl, and R 124 to R 127 adjacent substituents are linked to each other to form a substituted or unsubstituted fused ring, such as unsubstituted or alkyl-substituted fluorene, unsubstituted or alkyl-substituted dibenzothiophene, or unsubstituted or alkyl May form a dibenzofuran substituted with
R 201 to R 211 are each independently hydrogen, deuterium, halogen, unsubstituted or substituted (C1-C30) alkyl with halogen (s), substituted or unsubstituted (C3-C30) cycloalkyl. Or a substituted or unsubstituted (C6-C30) aryl, wherein adjacent substituents of R 208 to R 211 are linked to each other and substituted with a substituted or unsubstituted fused ring, for example, unsubstituted or alkyl Formed fluorenes, unsubstituted or alkyl-substituted dibenzothiophenes, or unsubstituted or alkyl-substituted dibenzofurans,
r and s each independently represent an integer of 1 to 3, and when r or s is an integer of 2 or more, each of R 100 may be the same or different;
e represents an integer of 1 to 3.
具体的には、リン光性ドーパント材料は、以下を含む。 Specifically, the phosphorescent dopant material includes:
本発明による有機電界発光デバイスは、アリールアミン系化合物及びスチリルアリールアミン系化合物からなる群から選択される少なくとも１つの化合物を有機層内にさらに含んでもよい。 The organic electroluminescent device according to the present invention may further include at least one compound selected from the group consisting of an arylamine compound and a styrylarylamine compound in the organic layer.
加えて、本発明による有機電界発光デバイスにおいて、有機層は、周期表の第１族金属、第２族金属、第４周期遷移金属、第５周期遷移金属、ランタニド、及びｄ遷移元素の有機金属からなる群から選択される少なくとも１つの金属、または該金属を含む少なくとも１つの錯体化合物をさらに含むことができる。 In addition, in the organic electroluminescent device according to the present invention, the organic layer includes an organic metal of Group 1 metal, Group 2 metal, 4th period transition metal, 5th period transition metal, lanthanide, and d transition element of the periodic table. It may further comprise at least one metal selected from the group consisting of, or at least one complex compound containing the metal.
本発明によると、カルコゲニド層、金属ハロゲン化物層、及び金属酸化物層から選択される少なくとも１つの層（以降、「表面層」）が、一方または両方の電極の内面（複数可）に配置されることが好ましい。具体的には、シリコンまたはアルミニウムのカルコゲニド（酸化物を含む）層が、好ましくは、電界発光媒体層のアノード表面に配置され、金属ハロゲン化物層または金属酸化物層が、好ましくは、電界発光媒体層のカソード表面に配置される。このような表面層は、有機電界発光デバイスの動作安定性をもたらす。好ましくは、該カルコゲニドは、ＳｉＯＸ（１≦Ｘ≦２）、ＡｌＯＸ（１≦Ｘ≦１．５）、ＳｉＯＮ、ＳｉＡｌＯＮ等を含み、該金属ハロゲン化物は、ＬｉＦ、ＭｇＦ２、ＣａＦ２、希土類金属フッ化物等を含み、該金属酸化物は、Ｃｓ２Ｏ、Ｌｉ２Ｏ、ＭｇＯ、ＳｒＯ、ＢａＯ、ＣａＯ等を含む。 According to the present invention, at least one layer (hereinafter “surface layer”) selected from a chalcogenide layer, a metal halide layer, and a metal oxide layer is disposed on the inner surface (s) of one or both electrodes. It is preferable. Specifically, a chalcogenide (including oxide) layer of silicon or aluminum is preferably disposed on the anode surface of the electroluminescent medium layer, and the metal halide layer or metal oxide layer is preferably an electroluminescent medium. Located on the cathode surface of the layer. Such a surface layer provides operational stability of the organic electroluminescent device. Preferably, the chalcogenide includes SiO X (1 ≦ X ≦ 2), AlO X (1 ≦ X ≦ 1.5), SiON, SiAlON, etc., and the metal halide includes LiF, MgF 2 , CaF 2 , The rare earth metal fluoride is included, and the metal oxide includes Cs 2 O, Li 2 O, MgO, SrO, BaO, CaO and the like.
アノードと発光層との間に、正孔注入層、正孔輸送層、電子阻止層、またはこれらの組み合わせが使用され得る。多層は、アノードから正孔輸送層もしくは電子阻止層への正孔注入障壁（または正孔注入電圧）を低下させるために、正孔注入層に使用され得る。２つの化合物が、各層内で同時に使用され得る。正孔輸送層及び電子阻止層もまた、多層で形成され得る。 A hole injection layer, a hole transport layer, an electron blocking layer, or a combination thereof can be used between the anode and the light emitting layer. Multilayers can be used in the hole injection layer to lower the hole injection barrier (or hole injection voltage) from the anode to the hole transport layer or electron blocking layer. Two compounds can be used simultaneously in each layer. The hole transport layer and the electron blocking layer can also be formed in multiple layers.
発光層とカソードとの間に、電子緩衝層、正孔阻止層、電子輸送層、もしくは電子注入層から選択されるか、またはこれらの組み合わせによって形成される層が使用され得る。多層は、電子の注入を制御し、発光層と電子注入層との間の界面特性を向上させるために、電子緩衝層に使用され得る。２つの化合物が、各層内で同時に使用され得る。正孔阻止層及び電子輸送層もまた、多層で形成され得、各層が２つ以上の化合物を含み得る。 Between the light emitting layer and the cathode, a layer selected from an electron buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof can be used. The multilayer can be used in an electron buffer layer to control electron injection and improve the interface properties between the light emitting layer and the electron injection layer. Two compounds can be used simultaneously in each layer. The hole blocking layer and the electron transport layer can also be formed in multiple layers, each layer including two or more compounds.
本発明による有機電界発光デバイスにおいて、電子輸送化合物と還元的ドーパントとの混合領域、または正孔輸送化合物と酸化的ドーパントとの混合領域が、好ましくは、一対の電極の少なくとも１つの表面上に配置される。この場合、電子輸送化合物が還元されてアニオンになり、それ故に混合領域から電界発光媒体までの電子の注入及び輸送が容易になる。さらに、正孔輸送化合物が酸化されてカチオンになり、それ故に混合領域から電界発光媒体までの正孔の注入及び輸送が容易になる。好ましくは、酸化的ドーパントとしては、様々なルイス酸及び受容体化合物が挙げられ、還元的ドーパントとしては、アルカリ金属、アルカリ金属化合物、アルカリ土類金属、希土類金属、及びこれらの混合物が挙げられる。還元的ドーパント層を電荷発生層として用いて、２つ以上の電界発光層を有し、かつ白色光を発する電界発光デバイスを調製することができる。 In the organic electroluminescent device according to the present invention, the mixed region of the electron transport compound and the reductive dopant or the mixed region of the hole transport compound and the oxidative dopant is preferably disposed on at least one surface of the pair of electrodes. Is done. In this case, the electron transport compound is reduced to an anion, thus facilitating the injection and transport of electrons from the mixed region to the electroluminescent medium. In addition, the hole transport compound is oxidized to cations, thus facilitating the injection and transport of holes from the mixed region to the electroluminescent medium. Preferably, oxidative dopants include various Lewis acids and acceptor compounds, and reductive dopants include alkali metals, alkali metal compounds, alkaline earth metals, rare earth metals, and mixtures thereof. An electroluminescent device having two or more electroluminescent layers and emitting white light can be prepared using the reductive dopant layer as a charge generation layer.
本発明の有機電界発光デバイスの各層を形成するために、真空蒸発法、スパッタリング法、プラズマ法、及びイオンめっき法等の乾式膜形成法、またはインクジェット印刷法、ノズル印刷法、スロットコーティング法、スピンコーティング法、ディップコーティング法、及びフローコーティング法等の湿式膜形成法が使用され得る。本発明の第１のホスト化合物及び第２のホストは、同時蒸着または混合物蒸着されてもよい。 In order to form each layer of the organic electroluminescent device of the present invention, a dry film forming method such as a vacuum evaporation method, a sputtering method, a plasma method, and an ion plating method, or an ink jet printing method, a nozzle printing method, a slot coating method, a spin Wet film forming methods such as coating methods, dip coating methods, and flow coating methods can be used. The first host compound and the second host of the present invention may be co-evaporated or mixture evaporated.
湿式膜形成法を使用する場合、各層を形成する材料を、エタノール、クロロホルム、テトラヒドロフラン、ジオキサン等の任意の好適な溶媒中に溶解または拡散させることによって、薄膜が形成され得る。この溶媒は、各層を形成する材料を溶解または拡散させることができ、かつ膜形成能力に問題のない、任意の溶媒であり得る。 When using a wet film forming method, a thin film can be formed by dissolving or diffusing the material forming each layer in any suitable solvent such as ethanol, chloroform, tetrahydrofuran, dioxane and the like. This solvent can be any solvent that can dissolve or diffuse the material forming each layer and does not have any problem in film-forming ability.
本明細書において、同時蒸着は、２つ以上の材料の各々をそれぞれの坩堝セルに導入し、蒸着させる材料の各々のセルに電流を印加することにより、２つ以上の材料を混合物として蒸着させるプロセスを示す。本明細書において、混合物蒸着は、蒸着前に１つの坩堝セル内で２つ以上の材料を混合し、蒸着させる混合物のセルに電流を印加することにより、２つ以上の材料を混合物として蒸着させるプロセスを示す。 As used herein, co-evaporation involves depositing two or more materials as a mixture by introducing each of two or more materials into a respective crucible cell and applying an electric current to each cell of the material to be deposited. Indicates the process. In the present specification, the mixture deposition is performed by mixing two or more materials in one crucible cell before the deposition, and applying two or more materials as a mixture by applying an electric current to the cell of the mixture to be deposited. Indicates the process.
本発明の有機電界発光デバイスを使用することにより、表示システムまたは照明システムを生産することができる。 By using the organic electroluminescent device of the present invention, a display system or a lighting system can be produced.
以降、以下の実施例を参照して、本発明のホスト化合物を含むデバイスの発光特性を詳細に説明する。 Hereinafter, the light emission characteristics of the device containing the host compound of the present invention will be described in detail with reference to the following examples.
デバイス実施例１：本発明の第１のホスト化合物及び第２のホスト化合物を含むＯＬＥＤデバイスの調製
本発明による有機電界発光化合物を使用して、ＯＬＥＤデバイスを生成した。有機発光ダイオード（ＯＬＥＤ）デバイス用のガラス基板上の透明電極酸化インジウムスズ（ＩＴＯ）薄膜（１０Ω／ｓｑ）（Ｇｅｏｍａｔｅｃ）を、アセトン、エタノール、及び蒸留水を連続して用いる超音波洗浄に供し、次いでイソプロパノール中に保管した。次いで、ＩＴＯ基板を真空蒸着装置の基板ホルダ上に載置した。ＨＩ−１を該真空蒸着装置のセルに導入し、次いで該装置のチャンバ内の圧力を１０−６トルに制御した。その後、このセルに電流を印加して上記の導入された材料を蒸着させ、それにより、８０ｎｍの厚さを有する第１の正孔注入層をＩＴＯ基板上に形成した。次に、ＨＩ−２を該真空蒸着装置の別のセルに導入し、このセルに電流を印加することにより蒸着させ、それにより、５ｎｍの厚さを有する第２の正孔注入層を第１の正孔注入層上に形成した。次いで、ＨＴ−１を該真空蒸着装置の別のセルに導入し、このセルに電流を印加することにより蒸着させ、それにより、１０ｎｍの厚さを有する第１の正孔輸送層を第２の正孔注入層上に形成した。次いで、ＨＴ−３を該真空蒸着装置の別のセルに導入し、このセルに電流を印加することにより蒸着させ、それにより、６０ｎｍの厚さを有する第２の正孔輸送層を第１の正孔輸送層上に形成した。化合物Ｈ−４４を、第１のホストとして該真空蒸着装置の１つのセルに導入し、化合物Ｈ２−１３２を、第２のホストとして別のセルに導入し、化合物Ｄ−９６を、ドーパントとして別のセルに導入した。２つのホスト材料をそれぞれ５０重量％の量にて同じ比率で蒸着させた一方、ホスト及びドーパントの合計量に基づいて４重量％のドーピング量でドーパントが蒸着して、同時蒸着し、３０ｎｍの厚さを有する発光層を第２の正孔輸送層上に形成するように、ホスト材料とは異なる比率でドーパントを蒸着させた。次いで、ＥＴ−１及びＥＩ−１を、それぞれ、真空蒸着装置の２つのセルに導入し、１：１の比率で蒸着させて、３０ｎｍの厚さを有する電子輸送層を発光層上に形成した。電子輸送層上に２ｎｍの厚さを有する電子注入層としてＥＩ−１を蒸着させた後、８０ｎｍの厚さを有するＡｌカソードを別の真空蒸着装置により蒸着させた。このように、ＯＬＥＤデバイスを生成した。
Device Example 1: Preparation of an OLED device comprising a first host compound and a second host compound of the present invention An organic electroluminescent compound according to the present invention was used to produce an OLED device. A transparent electrode indium tin oxide (ITO) thin film (10Ω / sq) (Geomatec) on a glass substrate for an organic light emitting diode (OLED) device is subjected to ultrasonic cleaning using acetone, ethanol, and distilled water successively, It was then stored in isopropanol. Next, the ITO substrate was placed on the substrate holder of the vacuum evaporation apparatus. HI-1 was introduced into the cell of the vacuum deposition apparatus and then the pressure in the chamber of the apparatus was controlled to 10 -6 Torr. Thereafter, a current was applied to the cell to deposit the introduced material, thereby forming a first hole injection layer having a thickness of 80 nm on the ITO substrate. Next, HI-2 is introduced into another cell of the vacuum deposition apparatus, and a current is applied to the cell to deposit it, whereby a second hole injection layer having a thickness of 5 nm is formed in the first cell. Formed on the hole injection layer. HT-1 is then introduced into another cell of the vacuum deposition apparatus and deposited by applying an electric current to the cell, thereby forming a first hole transport layer having a thickness of 10 nm in the second It formed on the positive hole injection layer. HT-3 is then introduced into another cell of the vacuum deposition apparatus and deposited by applying an electric current to the cell, thereby forming a second hole transport layer having a thickness of 60 nm in the first cell. It formed on the positive hole transport layer. Compound H-44 is introduced as a first host into one cell of the vacuum deposition apparatus, Compound H2-132 is introduced into another cell as a second host, and Compound D-96 is separated as a dopant. Introduced in the cell. The two host materials were each deposited in the same proportions in an amount of 50% by weight, while the dopant was deposited at a doping amount of 4% by weight based on the total amount of host and dopant, co-deposited, 30 nm thick In order to form a light emitting layer having a thickness on the second hole transport layer, a dopant was deposited at a ratio different from that of the host material. Next, ET-1 and EI-1 were respectively introduced into two cells of a vacuum vapor deposition apparatus and vapor-deposited at a ratio of 1: 1 to form an electron transport layer having a thickness of 30 nm on the light emitting layer. . After depositing EI-1 as an electron injection layer having a thickness of 2 nm on the electron transport layer, an Al cathode having a thickness of 80 nm was deposited by another vacuum deposition apparatus. Thus, an OLED device was generated.
生成されたＯＬＥＤデバイスは、５０００ｃｄ／ｍ２の輝度を有する赤色発光、及び４．９Ｖで２７．１ｃｄ／Ａの電流効率を示した。輝度が５，０００ニトで９５％に減少した期間は、４４時間以上であった。 The resulting OLED device showed red emission with a luminance of 5000 cd / m 2 and a current efficiency of 27.1 cd / A at 4.9V. The period when the luminance decreased to 95% at 5,000 nits was 44 hours or more.
デバイス実施例２：本発明の第１のホスト化合物及び第２のホスト化合物を含むＯＬＥＤデバイスの調製
デバイス実施例１と同じ様式でＯＬＥＤデバイスを生成したが、発光材料の第２のホストとして化合物Ｈ２−１５６を使用したことを除く。
Device Example 2: Preparation of an OLED device comprising a first host compound and a second host compound of the present invention An OLED device was produced in the same manner as Device Example 1, but compound H2 as the second host of the luminescent material Except for using -156.
生成されたＯＬＥＤデバイスは、５０００ｃｄ／ｍ２の輝度を有する赤色発光、及び５．４Ｖで２３．４ｃｄ／Ａの電流効率を示した。輝度が５，０００ニトで９５％に減少した期間は、１４７時間以上であった。 The resulting OLED device showed red emission with a luminance of 5000 cd / m 2 and a current efficiency of 23.4 cd / A at 5.4V. The period when the luminance was reduced to 95% at 5,000 nits was 147 hours or more.
デバイス実施例３：本発明の第１のホスト化合物及び第２のホスト化合物を含むＯＬＥＤデバイスの調製
デバイス実施例１と同じ様式でＯＬＥＤデバイスを生成したが、第２の正孔輸送層としてＨＴ−３の代わりにＨＴ−２を使用し、発光材料の第２のホストとして化合物Ｈ２−１６を使用したことを除く。
Device Example 3: Preparation of an OLED device comprising a first host compound and a second host compound of the present invention An OLED device was produced in the same manner as Device Example 1, but with HT- as the second hole transport layer. Except that HT-2 was used in place of 3, and compound H2-16 was used as the second host of the luminescent material.
生成されたＯＬＥＤデバイスは、５０００ｃｄ／ｍ２の輝度を有する赤色発光、及び５Ｖで２７．７ｃｄ／Ａの電流効率を示した。輝度が５，０００ニトで９５％に減少した期間は、２６時間以上であった。 The resulting OLED device showed red emission with a luminance of 5000 cd / m 2 and a current efficiency of 27.7 cd / A at 5V. The period when the luminance decreased to 95% at 5,000 nits was 26 hours or more.
デバイス実施例４：本発明の第１のホスト化合物及び第２のホスト化合物を含むＯＬＥＤデバイスの調製
デバイス実施例３と同じ様式でＯＬＥＤデバイスを生成したが、発光材料の第２のホストとして化合物Ｈ２−５１６を使用したことを除く。
Device Example 4: Preparation of an OLED device comprising a first host compound and a second host compound of the present invention An OLED device was produced in the same manner as Device Example 3, but compound H2 as the second host of the luminescent material Except for using -516.
生成されたＯＬＥＤデバイスは、５０００ｃｄ／ｍ２の輝度を有する赤色発光、及び４．７Ｖで２６．１ｃｄ／Ａの電流効率を示した。輝度が５，０００ニトで９５％に減少した期間は、２９時間以上であった。 The resulting OLED device showed red emission with a luminance of 5000 cd / m 2 and a current efficiency of 26.1 cd / A at 4.7V. The period when the luminance decreased to 95% at 5,000 nits was 29 hours or more.
デバイス実施例５：本発明の第１のホスト化合物及び第２のホスト化合物を含むＯＬＥＤデバイスの調製
デバイス実施例３と同じ様式でＯＬＥＤデバイスを生成したが、発光材料の第２のホストとして化合物Ｈ２−２１を使用したことを除く。
Device Example 5: Preparation of an OLED device comprising a first host compound and a second host compound of the present invention An OLED device was produced in the same manner as Device Example 3, but compound H2 as the second host of the luminescent material Except for using -21.
生成されたＯＬＥＤデバイスは、５０００ｃｄ／ｍ２の輝度を有する赤色発光、及び５．７Ｖで２６．７ｃｄ／Ａの電流効率を示した。輝度が５，０００ニトで９５％に減少した期間は、１６７時間以上であった。 The resulting OLED device showed red emission with a luminance of 5000 cd / m 2 and a current efficiency of 26.7 cd / A at 5.7V. The period during which the luminance decreased to 95% at 5,000 nits was 167 hours or more.
デバイス実施例６：本発明の第１のホスト化合物及び第２のホスト化合物を含むＯＬＥＤデバイスの調製
デバイス実施例３と同じ様式でＯＬＥＤデバイスを生成したが、発光材料の第２のホストとして化合物Ｈ２−４１を使用したことを除く。
Device Example 6: Preparation of an OLED device comprising a first host compound and a second host compound of the present invention An OLED device was produced in the same manner as Device Example 3, but the compound H2 as the second host of the luminescent material Except for using -41.
生成されたＯＬＥＤデバイスは、５０００ｃｄ／ｍ２の輝度を有する赤色発光、及び４．４Ｖで２７．０ｃｄ／Ａの電流効率を示した。輝度が５，０００ニトで９５％に減少した期間は、６４時間以上であった。 The resulting OLED device showed red emission with a luminance of 5000 cd / m 2 and a current efficiency of 27.0 cd / A at 4.4V. The period when the luminance decreased to 95% at 5,000 nits was 64 hours or more.
デバイス実施例７：本発明の第１のホスト化合物及び第２のホスト化合物を含むＯＬＥＤデバイスの調製
デバイス実施例３と同じ様式でＯＬＥＤデバイスを生成したが、発光材料の第２のホストとして化合物Ｈ２−４９５を使用したことを除く。
Device Example 7: Preparation of an OLED device comprising a first host compound and a second host compound of the present invention An OLED device was produced in the same manner as Device Example 3, but compound H2 as the second host of the luminescent material Except for using -495.
生成されたＯＬＥＤデバイスは、５０００ｃｄ／ｍ２の輝度を有する赤色発光、及び５．５Ｖで２５．１ｃｄ／Ａの電流効率を示した。輝度が５，０００ニトで９５％に減少した期間は、１０６時間以上であった。 The resulting OLED device showed red emission with a luminance of 5000 cd / m 2 and a current efficiency of 25.1 cd / A at 5.5V. The period during which the luminance decreased to 95% at 5,000 nits was 106 hours or more.
デバイス実施例８：本発明の第１のホスト化合物及び第２のホスト化合物を含むＯＬＥＤデバイスの調製
デバイス実施例３と同じ様式でＯＬＥＤデバイスを生成したが、発光材料の第２のホストとして化合物Ｈ２−１５４を使用したことを除く。
Device Example 8: Preparation of an OLED device comprising a first host compound and a second host compound of the present invention An OLED device was produced in the same manner as Device Example 3, but compound H2 as the second host of the luminescent material Except for using -154.
生成されたＯＬＥＤデバイスは、５０００ｃｄ／ｍ２の輝度を有する赤色発光、及び５．８Ｖで２５．８ｃｄ／Ａの電流効率を示した。輝度が５，０００ニトで９５％に減少した期間は、１０６時間以上であった。 The resulting OLED device showed red emission with a luminance of 5000 cd / m 2 and a current efficiency of 25.8 cd / A at 5.8V. The period during which the luminance decreased to 95% at 5,000 nits was 106 hours or more.
比較実施例：本発明の第１のホスト化合物のみをホストとして含むＯＬＥＤデバイスの調製
デバイス実施例３と同じ様式でＯＬＥＤデバイスを生成したが、第１のホストとして化合物Ｈ−４４のみを使用し、発光材料の第２のホストを使用しなかったことを除く。
Comparative Example: Preparation of an OLED Device Containing Only the First Host Compound of the Invention as a Host An OLED device was produced in the same manner as Device Example 3, but using only Compound H-44 as the first host, Except that a second host of luminescent material was not used.
生成されたＯＬＥＤデバイスは、５０００ｃｄ／ｍ２の輝度を有する赤色発光、及び５．７Ｖで２０ｃｄ／Ａの電流効率を示した。輝度が５，０００ニトで９５％に減少した期間は、１０時間以上であった。 The resulting OLED device showed red emission with a luminance of 5000 cd / m 2 and a current efficiency of 20 cd / A at 5.7V. The period when the luminance decreased to 95% at 5,000 nits was 10 hours or more.
本発明による複数のホストが使用されると、従来のデバイスと比較してより高い発光効率／出力効率及び大幅に改善された駆動寿命の効果がもたらされる。具体的には、高効率が高輝度で維持され、これは、ＵＨＤを必要とする近年の傾向において有利な特性である。 The use of multiple hosts according to the present invention results in higher luminous efficiency / output efficiency and greatly improved drive life compared to conventional devices. Specifically, high efficiency is maintained at high brightness, which is an advantageous property in recent trends that require UHD.
Claims (8)
Ｍは、二価金属を表し、
Ｙは、ＯまたはＳを表し、
Ｘは、ＮＲ９、Ｏ、またはＳを表し、
Ｒ１〜Ｒ９は、各々独立して、水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ６０）アルキル、置換もしくは非置換の（Ｃ３−Ｃ６０）シクロアルキル、置換もしくは非置換の（Ｃ６−Ｃ６０）アリール、置換もしくは非置換の４〜６０員ヘテロアリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換のジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のモノもしくはジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは、互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成し、
Ｍａは、置換もしくは非置換の５〜３０員窒素含有ヘテロアリールを表し、
Ｌａは、単結合、置換もしくは非置換の（Ｃ６−Ｃ３０）アリーレン、または置換もしくは非置換の３〜３０員ヘテロアリーレンを表し、
Ｘａ〜Ｘｈは、各々独立して、水素、重水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルケニル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルキニル、置換もしくは非置換の（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換の（Ｃ６−Ｃ６０）アリール、置換もしくは非置換の３〜３０員ヘテロアリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換のジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のモノもしくはジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、置換もしくは非置換の、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成し、
前記ヘテロアリール（エン）は、Ｂ、Ｎ、Ｏ、Ｓ、Ｓｉ、及びＰから選択される少なくとも１個のヘテロ原子を含有する、有機電界発光デバイス。 An organic electroluminescent device comprising at least one light emitting layer between an anode and a cathode, wherein the light emitting layer includes a host and a phosphorescent dopant, the host includes a plurality of host compounds, and the plurality of the plurality of host compounds At least the first host compound among the host compounds is a metal complex derivative represented by the following formula (1), and the second host compound is represented by the following formula (2):
M represents a divalent metal,
Y represents O or S;
X represents NR 9 , O, or S;
R 1 to R 9 are each independently hydrogen, halogen, cyano, substituted or unsubstituted (C1-C60) alkyl, substituted or unsubstituted (C3-C60) cycloalkyl, substituted or unsubstituted (C6 -C60) aryl, substituted or unsubstituted 4-60 membered heteroaryl, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted Di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, or substituted or unsubstituted mono- or di (C6-C30) arylamino Or at least one selected from nitrogen, oxygen, and sulfur in conjunction with each other Carbon atoms (s) may be replaced by a heteroatom, the monocyclic or polycyclic (C3-C30) to form an alicyclic ring or an aromatic ring,
Ma represents a substituted or unsubstituted 5- to 30-membered nitrogen-containing heteroaryl,
La represents a single bond, a substituted or unsubstituted (C6-C30) arylene, or a substituted or unsubstituted 3 to 30 membered heteroarylene,
Xa to Xh are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2 -C30) alkynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, substituted or unsubstituted tri (C1 -C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) Alkyldi (C6-C30) arylsilyl, or substituted or unsubstituted mono- or di (C6-C3) A substituted or unsubstituted, monocyclic ring that represents arylamino or is linked to each other and may be substituted with carbon atom (s) with at least one heteroatom selected from nitrogen, oxygen, and sulfur Forming a cyclic or polycyclic (C3-C30) alicyclic or aromatic ring,
The organic electroluminescent device, wherein the heteroaryl (ene) contains at least one heteroatom selected from B, N, O, S, Si, and P.
Ｍ、Ｙ、Ｘ、及びＲ１〜Ｒ８は、請求項１に定義されたとおりであり、
Ｒ１１〜Ｒ１８、Ｒ１’〜Ｒ８’、及びＲ１１’〜Ｒ１８’は、各々独立して、水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ６０）アルキル、置換もしくは非置換の（Ｃ３−Ｃ６０）シクロアルキル、置換もしくは非置換の（Ｃ６−Ｃ６０）アリール、置換もしくは非置換の４〜６０員ヘテロアリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換のジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のモノもしくはジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは、互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成する、請求項１に記載の有機電界発光デバイス。 Formula 1 is represented by one of the following formulas (3) to (8):
M, Y, X, and R 1 to R 8 are as defined in claim 1;
R 11 to R 18 , R 1 ′ to R 8 ′, and R 11 ′ to R 18 ′ are each independently hydrogen, halogen, cyano, substituted or unsubstituted (C1-C60) alkyl, substituted or non-substituted. Substituted (C3-C60) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted 4 to 60 membered heteroaryl, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or Unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl Or substituted or unsubstituted mono- or di (C6-C30) arylamino or linked to each other to form nitrogen Forming a monocyclic or polycyclic (C3-C30) alicyclic or aromatic ring, wherein the carbon atom (s) may be substituted with at least one heteroatom selected from oxygen, oxygen, and sulfur The organic electroluminescent device according to claim 1.
Ｍは、ＢｅまたはＺｎを表し、Ｙは、Ｏを表し、Ｘは、ＮＲ９、Ｏ、またはＳを表し、Ｒ１〜Ｒ９は、各々独立して、水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換の（Ｃ６−Ｃ３０）アリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは、互いと連結して、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成する、請求項１に記載の有機電界発光デバイス。 In formula (1),
M represents Be or Zn, Y represents O, X represents NR 9 , O, or S, and R 1 to R 9 each independently represent hydrogen, halogen, cyano, substituted or non-substituted Substituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, or Represents a substituted or unsubstituted di (C6-C30) arylamino or is linked to each other to form a monocyclic or polycyclic (C3-C30) alicyclic or aromatic ring, The organic electroluminescent device according to claim 1.
Ｌａは、単結合、カルバゾリレン、または次式（９）〜（２１）のうちの１つにより表され、
Ｘｉ〜Ｘｐは、各々独立して、水素、重水素、ハロゲン、シアノ、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルケニル、置換もしくは非置換の（Ｃ２−Ｃ３０）アルキニル、置換もしくは非置換の（Ｃ３−Ｃ３０）シクロアルキル、置換もしくは非置換の（Ｃ６−Ｃ６０）アリール、置換もしくは非置換の３〜３０員ヘテロアリール、置換もしくは非置換のトリ（Ｃ１−Ｃ３０）アルキルシリル、置換もしくは非置換のトリ（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換のジ（Ｃ１−Ｃ３０）アルキル（Ｃ６−Ｃ３０）アリールシリル、置換もしくは非置換の（Ｃ１−Ｃ３０）アルキルジ（Ｃ６−Ｃ３０）アリールシリル、または置換もしくは非置換のモノもしくはジ（Ｃ６−Ｃ３０）アリールアミノを表すか、あるいは互いと連結して、窒素、酸素、及び硫黄から選択される少なくとも１個のヘテロ原子で炭素原子（複数可）が置換され得る、置換もしくは非置換の、単環式もしくは多環式の（Ｃ３−Ｃ３０）脂環式環または芳香族環を形成する、請求項１に記載の有機電界発光デバイス。 In formula (2),
La is represented by a single bond, carbazolylene, or one of the following formulas (9) to (21):
Xi to Xp are each independently hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C2-C30) alkenyl, substituted or unsubstituted (C2 -C30) alkynyl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C6-C60) aryl, substituted or unsubstituted 3 to 30 membered heteroaryl, substituted or unsubstituted tri (C1 -C30) alkylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) Alkyldi (C6-C30) arylsilyl, or substituted or unsubstituted mono- or di (C6-C3) A substituted or unsubstituted, monocyclic ring that represents arylamino or is linked to each other and may be substituted with carbon atom (s) with at least one heteroatom selected from nitrogen, oxygen, and sulfur The organic electroluminescent device according to claim 1, which forms a formula or polycyclic (C3-C30) alicyclic ring or aromatic ring.
Ｍａは、置換もしくは非置換のピロリル、置換もしくは非置換のイミダゾリル、置換もしくは非置換のピラゾリル、置換もしくは非置換のトリアジニル、置換もしくは非置換のテトラジニル、置換もしくは非置換のトリアゾリル、置換もしくは非置換のテトラゾリル、置換もしくは非置換のピリジル、置換もしくは非置換のピラジニル、置換もしくは非置換のピリミジニル、及び置換もしくは非置換のピリダジニルからなる群から選択される単環式環型ヘテロアリール、または、置換もしくは非置換のベンズイミダゾリル、置換もしくは非置換のイソインドリル、置換もしくは非置換のインドリル、置換もしくは非置換のインダゾリル、置換もしくは非置換のベンゾチアジアゾリル、置換もしくは非置換のキノリル、置換もしくは非置換のイソキノリル、置換もしくは非置換のシンノリニル、置換もしくは非置換のキナゾリニル、置換もしくは非置換のナフチリジニル、置換もしくは非置換のキノキサリニル、置換もしくは非置換のカルバゾリル、及び置換もしくは非置換のフェナントリジニルからなる群から選択される縮合環型ヘテロアリールを表す、請求項１に記載の有機電界発光デバイス。 In formula (2),
Ma is substituted or unsubstituted pyrrolyl, substituted or unsubstituted imidazolyl, substituted or unsubstituted pyrazolyl, substituted or unsubstituted triazinyl, substituted or unsubstituted tetrazinyl, substituted or unsubstituted triazolyl, substituted or unsubstituted A monocyclic ring heteroaryl selected from the group consisting of tetrazolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted pyrazinyl, substituted or unsubstituted pyrimidinyl, and substituted or unsubstituted pyridazinyl, or substituted or unsubstituted Substituted benzimidazolyl, substituted or unsubstituted isoindolyl, substituted or unsubstituted indolyl, substituted or unsubstituted indazolyl, substituted or unsubstituted benzothiadiazolyl, substituted or unsubstituted quinolyl, substituted or unsubstituted The group consisting of quinolyl, substituted or unsubstituted cinnolinyl, substituted or unsubstituted quinazolinyl, substituted or unsubstituted naphthyridinyl, substituted or unsubstituted quinoxalinyl, substituted or unsubstituted carbazolyl, and substituted or unsubstituted phenanthridinyl The organic electroluminescent device according to claim 1, which represents a condensed ring type heteroaryl selected from:
Ｘａ〜Ｘｈは、各々独立して、水素、シアノ、置換もしくは非置換の（Ｃ６−Ｃ１５）アリール、置換もしくは非置換の１０〜２０員ヘテロアリール、または置換もしくは非置換のトリ（Ｃ６−Ｃ１０）アリールシリルを表すか、あるいは、互いと連結して、置換もしくは非置換の単環式もしくは多環式の（Ｃ６−Ｃ２０）芳香族環を形成する、請求項１に記載の有機電界発光デバイス。 In formula (2),
Xa to Xh are each independently hydrogen, cyano, substituted or unsubstituted (C6-C15) aryl, substituted or unsubstituted 10-20 membered heteroaryl, or substituted or unsubstituted tri (C6-C10). The organic electroluminescent device according to claim 1, which represents arylsilyl or is linked to each other to form a substituted or unsubstituted monocyclic or polycyclic (C6-C20) aromatic ring.
The compound represented by the formula (2) is:
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| KR102261645B1 (en) * | 2018-11-26 | 2021-06-08 | 삼성디스플레이 주식회사 | Heterocyclic compound and organic light emitting device comprising the same |
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| JP2010241801A (en) * | 2009-03-20 | 2010-10-28 | Semiconductor Energy Lab Co Ltd | Carbazole derivative comprising heteroaromatic ring, light emitting element, light emitting apparatus, and electronic equipment each employing the same |
| JP2012531383A (en) * | 2009-06-30 | 2012-12-10 | メルク パテント ゲーエムベーハー | Materials for organic electroluminescent devices |
| WO2012153725A1 (en) * | 2011-05-12 | 2012-11-15 | 東レ株式会社 | Light-emitting element material and light-emitting element |
Also Published As
| Publication number | Publication date |
|---|---|
| EP3207045A4 (en) | 2018-07-04 |
| WO2016060516A1 (en) | 2016-04-21 |
| CN106795166A (en) | 2017-05-31 |
| EP3207045A1 (en) | 2017-08-23 |
| US20170309841A1 (en) | 2017-10-26 |
| KR20160045604A (en) | 2016-04-27 |
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